Finally, The Encounter (Part 3)

Lovely tranny in teddy and some shiny pantyhose
What I recommend to a date (Flickr: The Poss)

This is part 3 of the tale of my first romp with a transvestite. Read part 1 for the prelude and part 2, the hookup.

Action time! I break out of my “disguise” of jeans and t-shirt to reveal my silky fuscia babydoll and Wolford pantyhose to the lovely Racquel. What a feeling of finally sharing my sexy girly side with another.

My girly cock was thinking the same thing too.

I lied down on her bed and caressed her black stockings with my hosed legs as she approached me. Then the unthinkable happened. She begins to strip down the Wolfords. Uh-oh, instant turn-off.

I don’t think Racquel particularly minded the lingerie and pantyhose (I believe she even called it “cute”) but only saw it as an obstacle to her real desire: get right to the cock.

Ok, so I know we’re not exactly two lesbians going at it but thoughts of manly gay sex began going through my head enough to cause a panic. I always envisioned myself a woman going at it with another hot woman, not two men who put aside their femininity to fuck.

In other words, the Wolfords and the babydoll had to stay on to preserve the “womanly” nature of the fucking.

Fortunately, Racquel played along, began to make fun of me (nicely) and pulled out a pink lace babydoll from her closet, then asked if I like it as she slipped it on. Actually she said, “Will this do, honey?”

Yes it will.

She quickly heads for the bed and begins kissing me while I feel up the stockings on her slim legs. Then, with her hands, pulls down my Wolfords enough to grab at my now-again raging cock. Wow. Truth be told, no genetic girl has ever sucked on it like that!

Just before I was about to climax, however, she stops, points to her own lady stick and demands from me the same treatment. I oblige. Keep in mind that this is my first blowjob, nevermind all the suck practice with a dildo in my bedroom.

I can’t say it was a real pleasure. Eyes watering, gagging and the endless spew of saliva from my mouth. I guess if you have to be broken in, this is what it takes. But just as I was worried that she was going to come in my mouth, she moves my head away. Relief.

“Turn around on your arms” she says. I knew what was coming next as she reached for a condom on the bed table.

She slowly pulls my pantyhose to just past my ass, begins to lube her girlish cock and gently whispers “relax, hon.”

While my first foray into felatio didn’t exactly go as I planned, nor left me turned on, I made no protests to the real deal about to go down. I reinforce to her that this is my first time, so go easy. The truth is, I don’t know whether she did or not but she went at it. And at it.

It maybe lasted five minutes but it felt like an eternity. Officially, I was broken in. Another bedpost notch for Racquel. My first official experience in the tranny world. Not exactly something I was proud of at that moment but I guess something that I had to get over with.

Then Racquel tells me it’s my turn as she grabs my cock and starts sucking. Somehow, while still in my non-aroused state, she manages to bring my cock back to life. Then she stops, turns around and points to her bed table. At this point, I stop, put my disguise of jeans and a t-shirt back on and politely explain that I needed to get out of there. Quickly, I exited.

I didn’t have a problem with Racquel. She was gorgeous by transvestite standards. Nor did I have a problem with going all the way (and then some) with her. My newly-defined sexuality wasn’t the issue either. It was just how I had went about it.

Too much, too fast? Likely. Something to contemplate as I walked home with a noticeably violated feel coming from my ass.

I believe this is called the walk of shame yet, with the “slutty” feel to it, was actually little refreshing.

2 Comments on “Finally, The Encounter (Part 3)

  1. I know just what you mean about maintaining the femininity, being a woman meant keeping the girly things on. I had the same problem too and my first experience like this gave me the same misgivings and mixed feelings as well. I was curious, excited and impatient about my first experience and I grew regretful at times over lack of condom use but I got lucky there ,more than once! I remember starting out at the club but getting a bit drunk and apparently I had said words to the effect that I wanted to go all the way and when I realized what was going on my saying “no” was not going to work. I certainly wasn’t going to call the police to say that I had been violated and he knew that. I do remember leaving his place and getting back to my car afterwards, the walk of shame is a perfect description although I admit I didn’t feel totally bad and to be honest a bit refreshed is a fabulous description.

  2. Oh you little slut 🙂

    Really though, the first experience should be an awkward one. Why have it any other way?

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